


Secretly?

by HyperKid



Category: Critical Role (Web Series)
Genre: F/F, F/M, Fluff, Gen, Guessing Games, M/M, Multi, Widojest week 2019, prompt: are you secretly in love with me, prompt: zone of truth, sleepy snuggles in a crystal cave, soft
Language: English
Status: Completed
Published: 2019-07-17
Updated: 2019-07-17
Packaged: 2020-06-29 23:48:43
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,796
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19841083
Author URL: https://archiveofourown.org/users/HyperKid/pseuds/HyperKid
Summary: An idle conversation turns into a game when Caleb remembers none of them know how old Jester is. And is promptly derailed by a certain tiefling.





	Secretly?

**Author's Note:**

> HK: Alright, things we learned this week?   
> Mollymauk: You’re terrible with deadlines and can’t be trusted?   
> HK: That I definitely jinxed myself way back last Monday! And, unfortunately, that I probably won’t have much of anything for BeauJes week. I’m crunching waaaay too hard for GenCon.   
> Mollymauk: You, not writing? That doesn’t seem realistic.   
> HK: Me not finishing anything in two weeks kinda does though?   
> Mollymauk: Well, so long as my coat looks ~fabulous~, I’m sure you’ll be forgiven.   
> HK: Will also be sloooowly working on a cuddle pile that’s nearly finished and another tiefling trickery, but I’ve got two coats to get done and so little time.   
> Mollymauk: Not like you’ve known for a year or anything.   
> HK: Shhhhh. 
> 
> WARNINGS!! Little bit of Caleb psyching himself out into panic mode? Nothing major 
> 
> Disclaimer: I own nothing, no one, and will not even be getting autographs because Of Course this is the year they don’t do them! What do you mean, “salty af”?

“We’ve really come a long way, huh?” 

Caleb glanced over, a brow raised slightly in inquiry. It had mostly been quiet since they settled down to sleep, safe in the hut inside a massive geode. Between the hut and Frumpkin no one had bothered to keep watch, though he knew the clerics had stayed up a while to enjoy the view. 

Caduceus had settled himself down to sleep not long after, and all had been silent in the hut. The soft colours of dancing lights reflecting off the crystals covered the dome in a sprinkle of glimmering reflections, more than enough light for him to write. He’d assumed Jester was sketching, or maybe just memorizing every detail to tell to the Traveler. 

But she sounded soft and pensive, and just a little bit sad. She was sat against the back curve beside him, their elbows not quite brushing in the close quarters. She had her knees tucked up close, arms around them as she gazed up at the ceiling. 

The wizard took a while to consider the question. He had to doubt she meant it geographically. 

“I suppose we have,” he mused eventually, his gaze drifting up to the ceiling too, “we have crossed the oceans, and now we are travelling to Xhorhas.” 

As expected, it brought a giggle from her and she leaned over just enough to nudge him.

“I didn’t mean the journey,” she teased, but it didn’t sound like a reprimand. Caleb nudged her back, a slight smile curling his lips. 

“I know. I just... when I was young, no one ever moved further from home than Rexxentrum. And even that was only the wealthy.” 

Beginning to understand, Jester’s mouth formed a perfect little o. She was quiet for a moment, considering his words. Then she nodded. 

“I think I see what you mean? When I was little I never really got to leave the house at all. I always dreamed of travelling, but not exactly as something I would ever do, you know?” 

Caleb nodded back, giving her a soft smile. 

“Yeah... pretty much. I feel like you can’t go so far without becoming a different person.” 

“A better person,” Jester agreed cheerfully, her fingers slipping across the ground to curl around his, “and definitely a happier person!” 

For a moment, Caleb wondered if she’d read his mind. The alternative was actually a little more disturbing for a change. Taking her hand in his, he raised it just a little, fingertips tracing across her skin. 

“Were you not happy before?” He asked. He couldn’t exactly imagine Jester being sad. As anything but the bright, bouncy cleric they had met in Trostenwold. It just didn’t seem... natural. 

Even Jester looked a little uncomfortable at the idea, her tail twisting itself into knots at her feet. 

“Well... I was, kind of. It was a lot of fun, growing up in the Chateau, and I love my mama and Blüd, and I always had the Traveler of course. But I was...” 

“Lonely?” Caleb offered, once the silence began to stretch. Jester shot him a sheepish grin. 

“Yeah. It’s been so nice to have people my own age around and getting to know all of you.” 

A drier, more darkly amused grin tugged at Caleb’s lips for a moment, but it brought with it a sudden realization. Someone her age... well. 

“How old are you, Jester?” He’d have to assume that he was a fair bit older than her, but honestly that came more from her bouncy, cheerful demeanour and her childish glee with the world. 

Both could just as easily have been the product of a more sheltered upbringing. And in her own way... sometimes Jester seemed a little wiser than them all. 

The tiefling shot him a very familiar grin, edged with mischief. 

“You still don’t know?” 

It was far too easy to lean in, to place a soft kiss to the corner of that damn grin. Jester turned into it, her lips brushing slowly over his, her grip tightening on his fingers for a brief happy squeeze. 

“How could I know, when you refuse to tell us?” He teased gently, drawing back just far enough to talk. He could feel her giggle gusting across his lips before she leaned in for another quick kiss and sat back. 

“But it’s so much more fun for you to try and guess.” 

“You just like making me feel old.” 

“I might~” Jester agreed with a playful flick of her tail, leaning back against the curve of the dome. Caleb sighed dramatically and leant back to match her, his spine bending forwards. 

“I suppose we should have some rules then, if we’re playing a guessing game. I wouldn’t want you cheating.” From the corner of his eye he could see Jester bounce happily, steepling her fingers and pressing them to her lips. 

“If there are no rules, how could I cheat?” 

He nudged her again, setting her knees bobbing. 

“You would find a way. So I think our first rule will be that you have to tell me the truth.” 

Jester pouted, fingertips tapping idly off her chin as she considered it. 

“Wellllllllllllll,” she dragged the word out, letting her head drop to one side, “I suppose... but then you have to tell me the truth too.” 

A warning jolt slammed up his spine and for a moment he thought something had triggered his alarm spell. A quick glance through Frumpkin’s eyes showed nothing though. It wasn’t exactly a relief. 

“What would you like me to tell the truth about?” He was amazed by how normal his voice sounded when his throat felt dry as parchment. Jester didn’t seem to notice, her tail twitching thoughtfully through question marks. 

It was something Frumpkin did when he was on the hunt. Not exactly comforting, but the similarity almost made him smile. 

Jester’s singsong voice dragged him back to the moment. 

“Well, I think I already know how old you are, kind of. And I know you don’t like to talk about your past. But we’ve done a whooooole lot over the time we’ve been together, and I do have some questions!” 

Still a little wary, Caleb watched her from the corner of his eye. 

“I would like to know what kind, before I agree...” 

“Of course!” Jester nodded happily, giving him a gentle nudge that was probably supposed to be reassuring. “Let’s see. I’d like to know more about how you and Nott broke out of prison. And which town we’ve been to you like best. And who of us you think is the cutest!” 

That managed to startle smile that was more than half relief from the wizard and he nodded slowly. 

“I suppose... as long as it is no more than that, I can promise you an honest answer.” 

Jester beamed and clapped her hands together, bouncing a little in place. 

“I promise! But how will I know you’re telling the truth?” 

This time Caleb nudged her, doing his best to fake being hurt. 

“Because I just told you I would be, Jester. Do you not trust me?” 

Tutting, the tiefling wrapped her arms around his arm, squeezing tightly. 

“Oh, Caleb, of course I trust you! But how will you know if I’m telling the truth?” 

Shifting lights from the crystals shimmered in her eyes, highlighting the points of each fang in her grin. Looking down at her for a moment Caleb couldn’t help thinking that this was probably what her Traveler looked like. Undistilled chaos. 

He gave her a light boop on the nose. 

“I could never hope to guess, Blueberry,” he told her solemnly as her eyes crossed to follow his finger. 

Jester laughed, turning her face into his shoulder to muffle the sound in the small space. There were a few sleepy grumbles from the rest of the Nein, but none stirred. For a moment, the tiefling stayed snuggled close, face pressed to the old coat she so loved to tease him about. 

Caleb let her stay, watching her as the tension bled slowly from his system. She’d respect his privacy. They all did. Even if he didn’t know why. 

When she looked up, there was a more playful smile on her face. 

“I do have this one trick the Traveler taught me. It makes it so that people can’t lie in a given space. We used to play Truth or Dare with it ages ago.” 

The spell struck a familiar chord with Caleb, for once not one that was immediately dark. Of being children at the Academy, working new spells into old games. 

He cut that train of thought off before it could go any further. 

“I think I have heard of such a spell? It was called a Zone of Truth.” 

Jester nodded happily, sitting up straight again to tuck herself up against his side, her feet tucked under her butt this time. It let her press that much closer, and Caleb slipped an arm around her shoulders. 

“Yeah, that sounds like the one! But you’ve got to promise you won’t resist it, okay?” 

For a moment, Caleb considered lying. Resisting the spell but letting her think he hadn’t, just in case. But... he wanted so badly to trust the Mighty Nein. To believe they could respect his privacy, safeguard his secrets even from themselves. 

He wanted to trust Jester. 

And he could always just not answer if she delved too deep. 

So he nodded, gave her a gentle squeeze, and she cast the spell. It buzzed over him like a cloud of static, tingling across skin and raising the hair on the back of his neck. Jester shivered a little against his side, then grinned up at him. 

“So, who wants to go first?” 

Caleb hesitated a moment, reservations dragging at his heels. 

“Do we need any more rules?” 

Jester pouted, considering again, and turned her head just enough to rest a horn on his shoulder. 

“I guess... nobody has to answer anything. And you can’t just ask boring questions like “how old are you, Jester?” Or “when were you born”. Okay?” Her fingers were stroking idly along the inside of his wrists now, skin to skin. It wasn’t the first time they’d touched by a long shot, but somehow without his wraps it felt more... intimate. 

He forced himself to think about her actual question, wondering if he should be obvious enough as to limit her questions to his time with the Mighty Nein. If she’d already know that was the line. 

Better to bring things back to the game. 

“And what do I get if I win?” 

It caught Jester by surprise and she straightened, puzzled frown turning into another grin. 

“If you win? If you can guess how old I am? Does that mean I win if you fail?” 

If he was thinking about winning and losing again, it meant he wasn’t worrying about the world falling down. That already made it a drastic improvement on before. 

The fact that Jester Lavorre hadn’t previously considered this something that could be won or lost was probably also telling, but the idea that she could was quite exciting. Especially if there were prizes to be claimed. 

Not quite following her train of thought but still ending at the same conclusion, Caleb pulled a face. Somehow, there was something a little more scary about Jester having won a favour from him than it should have been. There wasn’t much he wouldn’t do for the asking. 

Then again, at the moment he couldn’t think of anything she wouldn’t have done for the asking. So it would probably not be anything too bad either way. 

Put like that, Caleb grinned at her. 

“I think we will certainly have to have a prize. Especially since you cannot lie to me.” 

About to reply, Jester paused, remembered her own spell, and puffed up her cheeks in frustration. 

“Aww, shit. I didn’t think of that!” 

Caleb shrugged, giving her hip a brief squeeze. 

“I will also not be allowed to ask you directly, remember. But what should our prize be?” 

They both considered it for a while, Jester chewing on her lower lip while Caleb’s gaze drifted around the glimmering crystals of the cavern. Finally Jester spoke slowly, fingers curling around Caleb’s hair. 

“I dooooon’t think there’s anything special... I mean, we’ve pretty much all got what we have for a reason, right? So maaaaybe not a physical prize?” 

Something in her tone made Caleb suspicious in what was probably his favourite way; a slight smile tugged at his lips. 

“What did you have in mind?” He asked, like he didn’t already have a good idea of the answer. Jester’s grin was audible even without looking at her. 

“I wanna wear your book holsters for a day. Just to try them on. See if I like all the straps.” 

A shiver ran down Caleb’s spine, though whether it was from horror at the potential loss of his harness or from anticipation at Jester deciding she liked them was hard to tell. It also gave him some interesting ideas around what he could ask for. 

“Alright... and if I win?” 

Jester shrugged happily, her tail flicking to curl around one of his ankles. 

“I mean, that’s up to you. What would you like?” There was more than a hint of suggestion in her tone, and all Caleb could think about was her strapped in leather. Which was almost certainly her entire goal. 

As the pause lengthened Jester giggled, pleased with the effect she’d clearly had. Her tail flicked momentarily higher and paused, remembering that they weren’t exactly secluded in a tent anymore. Flicked again, deciding if she cared. 

Across the dome, Beau grumbled and rolled herself towards Yasha’s side. 

Jester let it go, resting her head against Caleb’s shoulder again. It served to snap the wizard out of whatever he’d been thinking about, but his voice was still ragged and raspy when he spoke. 

“That is... quite unfair if you aren’t going to follow through.” 

“Whoever said anything about not following through?” She teased lightly, walking her fingertips up and down one arm. “I’m just not doing it right now.” 

Caleb snorted a little louder than he’d meant to, prompting a set of low noises and shuffling from the rest of the Nein. And at the moment he had the benefit of knowing that she definitely meant it. He managed to regain some composure, half smirking. 

“Well... I think for my prize, you will have to give me your boots.” 

That caught Jester’s attention, both brows furrowing in confusion. 

“My boots?” 

“Your boots,” Caleb confirmed, digging his fingers in under her armpit where her armour couldn’t protect her from tickling. As she squirmed away, stifling laughter in both hands, Caleb settled back to the wall of the dome. “They’re nicer than mine, and you are cute when you’re hopping about.” 

It was a little more than he’d meant to say. He had to wonder if it was related to the effect of the spell she’d cast, though he was reasonably sure it couldn’t force an answer. 

Jester was happy enough to be called cute, peering down at the toes of her boots and clicking them together. 

“Well... will I get to wear yours?” 

Caleb considered it a moment, then shook his head. 

“No.” 

Jester whined in protest, swatting at his shoulder. 

“But what if the ground is sharp!” 

“I can carry you,” Caleb pointed out with a grin, leaning away and then back into her, the spell forcing him to add “at least for a little while.” 

That made her pause again, wheels turning behind her eyes as she worked out what he was actually asking her. Then she grinned. 

“I get them back if we’re in a fight?” 

Caleb shrugged, arm settling around her shoulders again. 

“If there is time. As I assume you’ll give my books back if I need them?” 

“Of course!” 

“Then I suppose we should begin.” 

*** 

It started innocuously enough, and Jester was true to her word. Her first questions were all about which towns he’d preferred, what his and Nott’s list of tricks held. And, of course, who in the Nein he thought was the prettiest. 

He tried to force himself to say Fjord at first, just for the look on her face, but the parameters of the spell caught him up. Fjord wasn’t pretty. 

Fjord was handsome, dashing, sexy, alluring, and downright adorable when he got all flustered, but he was a little too rugged to really pull off pretty. 

Jester, meanwhile... well, she fit it to a tee. Despite being strong enough to bench press pretty much any of them as she saw fit, she retained a delicacy, soft lines of her face and hair and sweet, welcoming smiles. If Caleb Widogast had written a dictionary, the only entry for pretty would have been Jester’s picture. 

Caduceus Clay was also extremely pretty, which made Caleb wonder if the extra softness in the word might just be a cleric thing. Beau would probably accept “handsome” as a compliment, but Caleb wouldn’t dare call her pretty for fear of her fists. Not from him, anyway. 

Jester got away with calling all of them pretty quite a lot, along with a fair few other things that no one else would be permitted to do. 

She probably also knew how strictly he stuck to the definitions of his words, and chose the one he felt would fit her best on purpose. She then followed it up by asking who he had the most fantasies about, and had to stuff her fist into her mouth to stifle delighted giggles when he’d very quietly admitted it was Caduceus. 

He had a certain interest in the firbolg that hadn’t yet been met half as much as his other companions. It pulled at his imagination. 

From his end, the questions began a little more benign. Unable to ask anything specifically pinning her to time, he’d been forced to cast his net a little wider. For a while he’d hoped the book of Nicodranas’ history might be of some help to him, but it had soon become evident that Jester wasn’t faking how little she’d been out as a child. 

She knew next to nothing of major civic events, and could only describe festivals by the noise and sights she’d had from her window. And one she had been escorted to by Blüd, but her excitement had more than chased away what the festival itself was for. 

Stuck for an answer, he’d wandered a little more widely in her past. Jester was a cheerfully open book, more than happy to talk about how long she’d known what her mother did, what kinds of things she’d witnessed in the Lavish Chateau, who her favourite people had been. 

After a little teasing, he’d asked her a few questions about the Nein as well, and not really been surprised by her answers. She was refreshingly candid, her heart on her sleeve in a way Caleb’s never really had been. Even as Bren, he’d kept his affections confined and his thoughts to himself. 

Jester rhapsodized happily about Yasha’s abs, long enough that Caleb was sure just the faintest hint of a blush came to the “sleeping” aasimar’s cheeks. She could easily name her favourite feature of every one of them, and declined to pick just one as a favourite to snuggle with. 

Why should she, when she fit so nicely right in the middle, and they could all pile up together? 

As they talked, keeping their voices low in deference to their sleeping companions, they kept slipping closer together. At one point, Jester slid all the way sideways until she was laying across Caleb’s lap, watching the reflections from the crystals shimmer across his face. 

It had gone past the game a while back, Caleb forgoing his actual goal just to ask her silly, fun questions. No matter how old Jester was, it wasn’t going to change anything. She was there, and she was his, every soft, sweet, bouncy inch of her. 

The way she smiled up at him, soft and sleepy as his hand stroked through her hair. The way she reached up to tug him down beside her. The way she shifted back so he could tuck himself in behind her, her tail wrapping around him to hold him close. 

There were no stakes that could possibly match any of that. However long they were travelling underground, whatever dangers they would face, there was nowhere in the world Caleb would rather have been than right where he was; surrounded by people who, for whatever reason, loved him. Surrounded by people he loved. 

And knowing that each and every one of them would agree, that it was their friendship and affection that led them from one place to the next. It was everything Jester had longed for as a child. Everything she’d imagined, part of every story the Traveler ever told her. 

Because what would be the point in travelling alone? She needed companions, stories to share. She needed someone to impress, someone to delight in her mischief when the Traveler wasn’t there. Someone to dry her tears, to hold her close, to sit up late into the night and play silly games with. 

She needed a cool head, someone who could tell her when was a good time for pranks and when to hold her peace. A steady hand at her back, ready when things got hard. 

Caleb slowly let the lights begin to fade as they descended into silence. As each blink lasted longer, costing more to open their eyes. Jester sighed softly, pressing a soft kiss to the top of his head. 

“Time to sleep now?” 

“I think so, Blueberry,” Caleb agreed in a low murmur, his own eyes falling shut as he pressed into the warmth of her chest. 

“That means I woooon~” Jester wasn’t quite too tired to tease yet, just a hint of triumph lacing her words. It made the wizard smile again and he nodded against her skin. 

“I think it does,” he agreed again. Jester hummed happily, tugging a blanket up and around them both with her tail. 

“I think I want one more question instead of your book harnesses, though.” 

That made him crack an eye open, a ghost of wariness ever present in his heart. 

“Oh?” 

The tiefling grinned, eyes and teeth just visible in the fading light of the spell. 

“Are you secretly in love with me?” She murmured against his hair as he settled in against her. Caleb glanced up, feeling the spell still in the back of his mind, and smiled. 

“No.” 

There was nothing secret about it. 

**Author's Note:**

> HK: I actually started this one with just the last sentence and no idea of how it was going to evolve from there, but I think I like it. Need more soft.


End file.
